Motley Fool Money – "Our Biggest Regret"

September 8, 2025

Episode Overview

This episode of Motley Fool Money centers on investing regrets—particularly ill-timed sells—and the lessons investors can glean from them. Host Rick Menaras is joined by regular analysts Jason Hall and Lou Whiteman. The team candidly shares their most painful sell decisions, examines why regret is unavoidable in investing, and then pivots to discuss stocks poised to benefit from potential market shifts in the near future. The episode’s tone is warm and conversational, blending personal anecdotes with actionable investing wisdom.

Key Discussion Points & Insights

1. Discussion of Biggest Investing Regrets

[00:00–06:39]

Lou Whiteman’s Regrets

• Lou admits he isn't the type to regret missing out on meteoric winners like Amazon or Tesla because he avoids high-flying early-stage stocks.
• Key regrets:
  • Exos Financial (online bank) – up ~200% since he sold
  • Lowe’s Financial/Hotel Conglomerate – almost a double since he sold
• Reason for the regret: He “sold them without any good reason,” simply because he was bored or distracted by shinier options.
  • Quote:

    “This is the danger of acting on the whim instead of with real intent.” (Lou, [01:46])

Jason Hall’s Regrets

• Tesla: Bought in 2016, sold for a small profit—now up 2,000% (Rule Breakers portfolio: 16,000%).
• Nvidia: Sold half two years ago—up 446% since, and “never been below the price I sold.”
• Microsoft: Sold in 2013 when Steve Ballmer left and Nadella replaced him.
  • Biggest regret: Selling Microsoft out of “impatience” at exactly the wrong time; since then, it’s become an 18-bagger.
  • Quote:

    “I sold entirely because I just ran out of patience at really the absolute wrong time to have been running out of patience with Microsoft.” (Jason Hall, [03:37])

Rick Menaras’s Hardest Regret

• Netflix: Bought 500 shares in 2002 (broken IPO). After splits, could have had 7,000 shares worth $8.7 million today but “sold 99% of my shares over 23 years.”
• Major sell: Offloaded 80% of Netflix shares “a couple of months into my shareholder tenure.”
  • Quote:

    “I have 100,000 bagger in my portfolio and it’s killing me.” (Rick, [03:53])

2. How to Avoid Investing Regrets

[04:37–06:39]

• Lou: It’s not about never selling—it’s about having a clear process and sound reasons.
  • “You have to have a reason. You have to have a process and stick with it.” (Lou, [04:44])
• Sell for valid reasons: thesis change, loss of conviction, funding life events.
• Avoid knee-jerk moves: Don’t chase shiny objects, and have a plan.
• Jason advocates for “regret minimization”—learn from mistakes, but don’t let them rule you.
  • Quote:

    “Making short-term decisions with long-term investments…that’s a lot of times the things that leads us to sell too soon.” (Jason, [05:45])

• Rick’s main takeaway:
  • “You should never buy a stock just because it goes down…and…you also shouldn’t sell a stock just because it goes up.” ([06:39])

3. Stocks to Watch for Rate-Cut Environment

[07:41–13:30]

Jason Hall on Starbucks (SBUX)

• Thesis: Opportunity well beyond rate cuts—a turnaround is underway.
  • Shares have been on a rough, volatile six-year streak with negative comps (comparable sales).
  • Cites Brian Niccol’s recent appointment as a possible catalyst.
  • “Positive momentum” and “exceptionally low expectations” set SBUX up to potentially beat in the next quarter.
  • Quote:

    “Starbucks looks like it’s finally working through years of problems that have hurt the business. […] There have been signs of life.” (Jason, [08:39]–[09:35])

Lou Whiteman on Montrose Environmental (MEG)

• Thesis: Rate cuts could help, but the business is compelling on its own.
  • This small-cap environmental services roll-up is leveraged but has room to grow if debt costs fall.
  • They offer water and air quality monitoring and hold a slate of patents in microplastics cleanup.
  • Their consolidation strategy enables them to serve large, national clients.
  • Quotes:

    “[Montrose] provide necessary services—environmental cleanup and monitoring. These are long-term needs.” (Lou, [10:55])
    “Find a consolidator in a fragmented sector, and you can make a lot of money that way.” (Rick, [12:14])

Rick Menaras on Zillow Group (ZG)

• Thesis: As rates fall, housing market activity will revive, benefiting Zillow’s portal and ad revenue.
  • 243 million average monthly users makes it a market leader.
  • “Zillow lights the housewarming candle on both ends”—more buyers, more sellers, both increase advertising demand.
  • Revenue and earnings growth have returned, though the stock is flat over five years.
  • Quote:

    “Zillow is back to posting double digit revenue growth…and adjusted earnings is growing even faster. It’s doing well now. It should really be doing well a few months from now.” (Rick, [13:21])

4. Game – Double Trouble

[14:56–17:58] (A rapid-fire quiz on which stocks have doubled or halved in 2025, with playful banter and insight.)

• Freshpet (FRPT): Trouble; down 63% ([15:30])
• Wayfair (W): Double; up 103% ([15:59])
• Banco Santander (SAN): Double; up 110% ([16:34])
• C3AI (AI): Trouble; down 55% due to widening losses and declining revenue ([16:59])
• Newegg Commerce (NEGG): Double; up 452%, riding the meme-stock wave ([17:33])

Humor highlight – speculation on whether the trio could make a good boy band.

Memorable Quotes & Moments

• “This is the danger of acting on the whim instead of with real intent.” —Lou Whiteman [01:46]
• “I sold entirely because I just ran out of patience at really the absolute wrong time to have been running out of patience with Microsoft.” —Jason Hall [03:37]
• “I have 100,000 bagger in my portfolio and it’s killing me.” —Rick Menaras [03:53]
• “It’s part of the process and hopefully sharing these stories with others that have made mistakes…helps you out a little bit too.” —Jason Hall [06:20]
• “Never buy a stock just because it goes down…likewise, don’t sell just because it goes up.” —Rick Menaras [06:39]
• “Find a consolidator in a fragmented sector, and you can make a lot of money that way.” —Rick Menaras [12:14]

Timestamps of Notable Segments

• 00:00–03:53: Personal stories of biggest selling regrets
• 04:37–06:39: How to minimize regret and improve sell discipline
• 07:41–13:30: Featured stocks for a rate-cut environment: Starbucks, Montrose Environmental, Zillow
• 14:56–17:58: “Double Trouble” stock performance game

Episode Takeaways

• The most costly mistakes for investors often stem not from sell decisions due to valid concerns, but from selling on whim, impatience, or boredom.
• Regret in investing is unavoidable, but developing and sticking to a process can dramatically reduce painful errors.
• Preparedness for market cycles, concentration risk, and rebalancing are part of being a disciplined investor.
• The episode combines relatable tales of loss with optimism about future opportunities.

For More

• Don’t miss the playful “boy band” jokes woven throughout the episode.
• The full discussion is spiced with practical advice and humor, characteristic of Motley Fool Money’s tone.

Disclaimer: Speakers and The Motley Fool may have positions in the discussed stocks. Always do your own research before investing.